


50 Shades of a Moose's Lover

by gracestealingcastiel



Category: Supernatural
Genre: F/M, M/M
Language: English
Status: In-Progress
Published: 2014-08-16
Updated: 2016-04-24
Packaged: 2018-02-13 09:09:41
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 12
Words: 18,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2145072
Author URL: https://archiveofourown.org/users/gracestealingcastiel/pseuds/gracestealingcastiel
Summary: <blockquote class="userstuff">
              <p>Sam meets a mysterious CEO while helping his brother with an article. [LOOSELY BASED OFF OF 50 SHADES OF GREY. I DO NOT OWN 50 SHADES OF GREY OR ANYTHING TO DO WITH IT!]</p>
            </blockquote>





	1. Chapter 1

Sam took in a breath and let it out slowly as he paced in front of a large building. He shouldn't of told Dean he’d help him with this stupid article, he should have let the sick man lay in his bed and whine like a baby. “God I hate you Dean.” He muttered to himself and let out a breath and walked into the building. Walking into the lobby Sam was wearing a lot of his brother’s clothes, his brothers pressed dark blue button up shirt with his tweed waistcoat and matching suit jacket. Running his hands through his hair he walked up to the reception desk and smiled. “Hi there I’m Dean Winchester’s replacement, I’m Sam Winchester, I’m here to interview Gabriel Novak?” He smiled at the woman as well as he could to hide his nervous state and the woman smiled. The woman was a dark brunette with beautiful hazel green eyes. “Of course Mr. Winchester, please” She held up a name tag for the man and he laughed. “Right...right.” he grabbed the badge and clipped it to one of the pockets on his waistcoat and raised his eyebrows quickly. “When will he be ready for his interview?”

The woman smiled. “Come with me.” Sam followed behind the woman and realized the woman was wearing a pencil skirt and a well fitted pressed dress shirt. Well the man did own several businesses….he was a jack of all trades from what he heard. Gabriel Novak, he had his fingers in everything. Looking down at the note pad he saw some of his brother’s scribbles and quickly started to scratch out ‘total hunk’ and ‘possibly fuckable’ “Great...that’s just great Dean.” He muttered to himself and the woman turned and raised an eyebrow. “I’m sorry did you say something and Sam’s face went a dark red and he shook his head “No no..”

The woman smiled “Don’t be so nervous..” She pressed the only button beside an elevator and the doors opened with a soft ding. “Stick to you script.” she smiled as the doors closed and once Sam was alone he could finally breathe again. What was it about the slow agonizing trip in an elevator that made his stress levels go straight through the roof. Shaking his head he ran his hands through his hair once more checking his reflection in the mirrored walls and stepped out when the doors opened.

Gabriel’s office, or at least his reception office was very bold. Dark Maroon’s and bright whites it was inviting in a very seductive way and not really what he pictured an office to be at all. Walking in he noticed another brunette with bright hazel green eyes sitting behind the desk. He blinked and bit his lower lip suddenly he wondered if Mr. Novak had a thing for brunettes with green eyes. Sam also made a note that all the girls were natural brunettes and not dye jobs. Sam inwardly kicked himself in the butt for even being able to tell the difference.

“Hello there, you must be Sam Winchester, I’m Becky I’m Mr. Novak’s assistant. Can I get you anything? Soda? Water? Perhaps some tea you look a little shaky,” She smiled and took the man’s arm and lead him into a chair. “You should relax, I’ll be right back with a drink, is this your first corporate interview?” 

Sam blinked “Well I’m not really...Oh I don’t need anything to..” but the woman was gone and he sighed and blew some hair out of his face. “Come on Sam pull yourself together.” He sighed and shook his head. When Sam heard steps coming his way he stood up to tell the woman he was okay but instead of a brunette walking his way there was a short man with thick golden brown hair and dark hazel eyes. His suit was a black and he wore a blue waist coat, white shirt and no tie. “Hello there, you must be Samuel Winchester.” He held out the mug to Sam and Sam blinked just staring at the mug for a minute before he reached out quickly and took it. “Thank...Thank you sir I’m sorry I…” Gabriel smirked snorting a little. “You know you young ones with your Google machine I’d expect you to know everything about me...I’m Gabriel Novak” 

Sam’s eyes went wide and he dropped the mug to shake the man’s hand and hot tea splashed up his leg and Sam gasped jumping. “Shit..oh shit I am so sorry!” He could see the tea instantly staining the man’s pure white carpet. “I am so sorry I can pay for that I can - “ Gabriel laughed and shook his head. “No no, it’s fine it’s….come on, why don’t we head into my office and we can start the interview.”

Sam walked behind Gabriel his face as red as the walls in the man’s reception office, he felt like he was going to be sick and he was sure that Dean was going to kill him when he heard how the interview went. 

_Just stick with the script dummy, don’t screw this up this is supposed to be your brother’s  
crown piece for the month. _

Walking into a large office Sam was yet again blown away, wall to wall windows and the only walls were that familiar maroon red that was also in the reception office. “Here, take a seat.” Gabe smiled and pulled out a chair and Sam walked over to it and sat down and Gabriel perched himself up on the edge of his desk and looked down at Sam, his lips pulling ever so slightly in a smile. “How can I help you Sam?” 

Oh god that smile, is that why Dean sent Sam this way? Because of that smile? Sam found himself staring at the man and his face went a horrible shade of red. “Uh, well I have a few questions for you. I know you were expecting my brother Dean but he has a cold so...I’ll just be doing the interview is that okay?” Gabe nodded and stood up pulling off his jacket and hung it on the back of his chair. “Yes of course, go ahead and ask your questions.” He sat at his desk and looked across over at Sam. The man nodded and his mouth went dry and he blinked “Um, would it be possible to have a glass of water I…” Gabe smirked again and picked up his phone and whispered into it. A minute later Becky from the desk walked up and put a cup on the table beside Sam.

“Thank you” he looked up at Becky but she was already out the door. He looked back at Gabriel and looked down at the note book in his hand and took in a breath. “Okay Mr.Novak, I just have some questions.”

“Call me Gabriel…”

“Okay...Gabriel, you’ve got one of the most extensive empires for someone under the age of 40, what’s the secret to your success.” 

Gaberiel smiled “You really want to know?”

Sam nodded and the man leaned across his desk. “Total and complete control over everything that goes down in every aspect of everything I touch...everything. Complete and total control.”


	2. Who's Gabriel Novak?

**Summary for the Chapter:**

> Gabriel finds Sam at his place of work after the interview, Sam starts to wonder why the man searched him out...or was it just a coincidence.

Sam pushed through the door of the apartment he shared with his brother and shivered from the temperature difference. The apartment was a lot warmer than the rest of the building and it made Sam remember that his brother really was sick. “Dean are you alive?” Sam spoke up as he walked in and threw his jacket on one of the chairs that sat around their small table in their walk in of a kitchen. Walking into the living room he saw his brother staring at the t.v. with a blanket wrapped around him looking like a zombie. 

“Are you even alive?” Sam blinked and he saw his brother blink and quickly come to life sitting up. “What? Yes of course I’m alive, shut up Sammy..” He blinked and rubbed his face with his hands and looked over at the man. “Wait did you do it? Did you do the interview…” Sam nodded and put the notebook and the recorder on the coffee table in front of them. “There’s the entire thing, I tried to stick to the script but Gabriel likes to talk.”

Dean sniffled and then grabbed the notebook and started to read the man’s notes. “Your on a first name basis with one of the most rich and powerful men in the city? Brava brother, brava.” Dean muttered and raised an eye when he saw a line underlined. “Why did you underline that Gabriel likes to be in control of everything? Were you guys ….were you hitting on him during the interview? Sam I told you to keep to yourself!”

Sam blinked “Oy! No I was proper good like you told me to be!”

Dean looked over the notes “Yeah well I just hope that he doesn’t tell my boss that I was sick and sent some dick squeeze in my place.” Sam rolled his eyes and got up “You know your a real baby when you have a cold.” Sam shook his head and Dean laughed a little before he started to cough. “Speaking of which can you make me soup...Sam? Sammy?” Dean looked back over his shoulder as his brother walked into his bedroom.

“Come on Sammy I’m sick! Take care of your big brother.”

“I’d rather not, I already did you a favour today and it almost killed me.” Sam shouted back from where he laid on his bed.

Dean wrapped himself in a blanket and walked over to the man’s door and pushed it open with his foot. “Oh come on he’s not that intimidating is he?” Sam looked up at his brother. “The man screamed sexuality! It was torture…” 

Dean laughed “Oh my baby brother, just hungry for the d.” Dean waddled away to make himself soup and Sam threw a pillow at his door to shut it behind his brother and sighed staring up at the ceiling of his bedroom. The man really did ooze sexuality in every word he said and in everything he did, it made Sam almost uncomfortable.

But thankfully for Sam the next day he went back to his regular day job of working at a coffee shop. It wasn’t a very great job but it was keeping up with the bills and one day his acting would come together and he’d be able to get the hell out of the coffee business. 

“Hey Sam, can you grab some more decafe beans we’re out!” Jessica screamed from the front counter. Sam was in the back doing dishes and wiped his hands on his dark green apron and sighed. “Sure thing Jess” Liz was a short dumpy blond haired girl with freckles and bright green eyes. On many occasions Sam and Jess would work late nights doing the inventory for the entire place. Sam had taken the girl on a few dates in the past before he realized the girl just wasn’t for him. Of course they hadn’t had that conversation yet...Sam was trying to put it off until he finally could leave this place.

Walking through the small kitchen he walked into the one dry storage closet and walked to the back of the long narrow closet and grabbed the decaf beans from the top shelf. When he turned around Jessica was standing there with a smile on her face. “So you know...there isn’t any camera’s in the stock room.

Sam laughed shortly “Yeah I uh...I know but we can’t do this now Jessica, there’s other people here.”

Jessica smiled “What I can’t even get a quick kiss? Not even a small one…” Sam looked down at her before looking around and sighed giving the girl a quick kiss on the forehead he squeezed past her and pushed open the stock room door to see Liz, another one of the coffee house workers standing there. Liz was Jessica’s best friend and probably knew everything. Liz raised a thick eyebrow at the man and her blue eyes twinkled. “Sam..there’s a guy in a suit here for you.. I think your brother has finally be institutionalized.” Sam pushed past the girl. “Ha ha Liz, just because Dean isn’t into you doesn’t make him insane.” He heard the girls voice behind him but didn’t pay attention to the words. Walking out ot the counter he saw Gabriel standing there and dropped the bag of beans he was holding. “Mr. Novak?” Gabriel slipped his hands out of his pockets and rubbed them together. “What did I tell you about calling me that Sam?” He smiled slightly and Sam could feel his face growing hot. He also knew that Liz and Jessica were staring at him and he gave the two girls a quick look before walking up to the register. “Um...could I help you?”

Gabriel looked up at the menu confused. “I don’t normally go to these types of places...what do you suggest?”

Sam froze in place and blinked, if the man didn’t go to places like this then why was he there? Oh god was the man hunting Sam down? Did Sam do something he wasn’t supposed to? Or worse was the man interested in Sam? Sam didn’t know if he could handle a man like Gabriel Novak...who on this earth could handle a man like Gabriel Novak.

“I like the caramel frappuccinos…” He whispered and cleared his throat. “Would you like me to make you one?” He spoke up a little and Gabriel stared at the two women behind him. “Could one of you please make me one? Any size it doesn’t matter…” The girls both stared at Gabriel in disbelief before they walked off together their voices high pitched and quick paced. Sam quickly looked back at the girls before he looked at Gabriel and the man smiled “I hope I didn’t just get you in trouble” Sam laughed “Nah they couldn’t give me trouble in they wanted to, they need me to much.” Gabriel smiled and then there was a caramel drink thrown between them and Sam blinked “That’ll be seven fifty five.” 

Gabriel put a ten dollar bill on the counter and smiled “You can keep the change..” He whispered and looked up at the tall man. “You are a very interesting man Sam Winchester” Sam blinked “I am?” Gabriel smirked and nodded “OH yes...I’ll be seeing you again…” He walked out of the coffee shop and the man turned and saw two very angry women staring at him. “What?”

“You and Gabriel Novak?!” Liz screeched and Jessica blinked. “Who’s Gabriel Novak?”


	3. Realization

**Summary for the Chapter:**

> Sam has another run in with Gabriel Novak and things are starting to unravel around him. Since when did Gabriel Novak have such an impact on his life?

Seeing Gabriel at the coffee shop threw Sam for a loop, did the man purposefully go out of his way to find him? Why? It drove Sam crazy as he drove home, his mind going over the meeting over and over again trying to think of what he could have missed. When he got home he frowned when he saw someone parked in his spot. He sighed and parked in guest parking. “Damnit Dean.” He muttered and got out of the car and head upstairs to his apartment and heard a familiar voice on the other side of the door. Pushing it open he saw Jessica sitting beside Dean who was showing her the article that Sam helped him write. “Oh hey Sammy” Dean looked up and gave a side glance over to the blond beside him and Sam sighed. “Hey Dean…” He walked past the both of them and headed to his room and Jessica stood up. “Hey Sam, a bunch of us are going to the bar tonight I thought maybe you’d like to come with us. Dean said he’d come…” She smiled hopefully.

Sam looked over at Jessica and sighed, for years the girl had tried to get him to go out with her. It wasn’t that Sam didn’t find the girl attractive it had nothing to do with it. She was beautiful and he’d be lucky to be with her but there was just something...there was no spark between them. “I don’t know Jessica….I mean I open tomorrow and..” he started to rub at his arm and Dean groaned. “No, he’s going Jessica don’t worry, Sam needs to get out of the house once in a while and if I have to drag him out kicking and screaming I will.” Sam blinked and stared at his brother. “Are you serious right now?” Dean blinked “Your damn right I’m serious! You can’t stay inside every night it’s not right it’s just one night come on.”

Sam shook his head and sighed. “Fine...fine I”ll go take a shower and...get some food together to eat.”

Dean smirked ‘Don’t worry about that I’ve got take out on it’s way.” Sam rolled his eyes “Of course you do.” he sighed and walked towards the bathroom grabbing a towel on the way. Dean had been trying to set him up with every girl they knew for the past year. The man didn’t understand that Sam needed more than just a physical attraction to someone to be in a relationship with them. He didn’t know what it was but ...he just had no interest to be with anyone. Sam took an overly long shower while he heard Dean and Jessica eating out in the kitchen. When he finally did emerge from the bathroom he was wearing a black t-shirt and a pair of blue jeans that hugged him in all the right places, not that he cared. Running his hands through his flowing locks he shook his head and Dean moaned. “Damnit Sam your not a dog come on!” Dean wiped his face with his hands and Sam laughed “That’s what you get for making me get ready to get out.” He saw the pizza and walked over and saw Jessica staring at him and he felt uncomfortable.

“So who else is coming to the bar tonight?”

Jessica shrugged “Everyone from the coffee shop and a few other people. Jo is coming too, apparently she’s got some news to share.” Sam looked over at Dean quickly and saw the man’s face pale a little. “Still wanna go?” Sam looked at Dean and winked, Dean growled. “It isn’t like that anymore man we can be in the same room for more than five minutes without fighting.” Sam shrugged “Okay Dean whatever you say.” He bit into his piece and smiled.

It didn’t feel like very long until Sam was surrounded by people he didn’t feel like seeing and sighed into his beer. “I didn’t even wanna be here.” He muttered, looking around the bar he blinked when he saw Gabriel Novak walk in and his jaw dropped a little. Dean appeared at his side and he gasped “Oh you dog you totally have the hots for Gabriel Novak I knew it! I invited him you should go say hi” Dean pushed the man towards the shorter golden brunette. Sam looked back at Dean and slowly walked away from his brother before he walked up to Gabriel. “What’s a guy like you doing in a dive like this?” He smirked and he saw Gabriel look up at him with dark eyes and Sam felt weak. “I mean…..I’m sorry” Sam sputtered and Gabriel looked past Sam and blinked. “I don’t think she’s very happy, your friend?” Sam turned and saw Jessica standing there with a bottle of beer in her hand. Tears welling up in her hand Sam looked back at Gabriel and held up a finger before he walked over to Jessica. “I think it’s time for you to go home Jess you look trashed.”

“Your hot for that guy aren’t you, what’s wrong with me?”

Sam blinked and sighed “Jessica your drunk come on please let me get you a cab.”

“What did I do? Why don’t you like me Sam.” She looked up at him and Sam looked at her before he looked over at Gabriel. “It’s not like that Jess come on please let’s not make a scene.” He took the beer from her hand and put it on the table and took her elbow and tried to push her out. As they got close to Gabriel Jessica pulled away from Sam and pointed at the man. “You took away the man I love! You better not hurt him...he’s pure sunshine, he deserves ...gold” Jessica sniffed and Sam’s face turned a crimson as he quickly shook his head and pulled the girl away. “Jessica come on.” 

Sam finally managed to get the girl outside and he pushed her against the wall. ‘Stay here Jess...don’t talk to anyone.” Same walked up to the sidewalk and smiled, for once his tall stature was good for something. When he waved his large arm through the air a cab drove over and he turned back to see Gabriel whispering into the girl’s ear. Jessica’s face was red and she was nodding clearly sputtering. Sam quickly moved to her side and took her elbow. “I got you a cab Jessica….come on.” He gave Gabriel a sympathetic look before he guided her into a cab and licked his lip, he should make sure she got home fine.

“I’ll be fine, have fun.” Jessica muttered and climbed into the car closing the door behind her which sent Sam stumbling back a step as the cab drove off. He looked back and saw Gabe with that slight smile on his face hands in his pockets. 

“What...what did you say to her?” Sam looked over at the man who shrugged “ I might have told her that I am more than capable of making sure you have a good time tonight and she shouldn’t worry. I’m not stealing you away unless you want me to.” Sam could have died right there on the spot but instead he tried to keep his heart beat steady so he didn’t blush. Slowly Gabriel walked towards the man. “Sam...I believe you are blushing...should I buy you a drink?” Sam blinked “Wh….why I mean I’m just a ….you don’t want me you have so many beautiful women you could choose from.” Gabriel pulled the man down to his height and whispered into his ear. “That’s the problem, they’re not you.” Sam took in a breath and let it out and shook his head “I should go check on my brother.” Gabriel watched Sam walk into the bar and he sighed and walked towards his car.

Sam walked into the bar and saw a dark haired man dancing with his brother and blinked. “Dean?” He walked over and tapped Dean’s shoulder “Hey what’s going on!” He looked past Dean at the blue eyed brunette and Dean laughed. “Oh hey! Where’d Gabriel go?” The man suddenly blinked. “Gabriel’s gone? I’ve gotta go” The man quickly ran off and Dean moaned “No...don’t go.” He looked over at Sam. “What did you do Sammy?”

Sam blinked “I don’t understand what your talking about.”

“I had a hot man who wanted to take me home and you ruined it..where’s Jessica.”

Sam blinked “I put her in a cab..”

Dean growled. “Fine let’s go..” 

Wait...when was Dean into men?


	4. Take me out, tonight

**Summary for the Chapter:**

> Another run in with Gabriel Novak ends in a date, is Sam nervous?

The next few days Sam spent his days at the coffee shop waiting for Gabriel to come waltzing back into his life. He really hoped that he hadn’t shoved the man away when he chose checking on his brother over going away with him but...really what did Gabriel expect? Sam wasn’t drunk and even if he was he wasn’t going to just go off with the man. The man could have anyone he wanted why would he want him? Sam moaned and rubbed his face when the coffee shop died a little.

“Your burning the milk” Jessica pointed at his hand and Sam jumped sending the small mug in his hand flying and he groaned. “Fuck off..” he sighed and bent over and started to clean it up. After a moment Jessica was down on the ground beside him. “Fix your hair, and slowly stand up” She whispered to the man and Sam stared at her “What?” and Jessica mouthed ‘just do it’. Taking in a breath Sam ran his hands through his hair smoothing it out the best he could and stood up and saw Gabriel Novak standing there. “Gabriel...um, how can I help you?” Gabriel stared at the man and took in a breath. “For the past ten years, I’ve always gotten what I’ve wanted. If I wanted to take over a business, I did, and if I wanted to buy real estate I did...you are the first thing in a very long time that I haven’t gotten when I wanted. That frustrates me.” 

Sam blinked shocked that the man was this open in public he looked around and realized that the shop was empty except for him, Jessica and Gabriel anyway. “Um, I don’t know what that means.” Gabriel smirked ever so slightly and Sam felt his knees go weak and his jeans grow tight. “That means Mr. Winchester...let me take you out for dinner. If you do not enjoy yourself….then I will leave you alone and you will never have to talk to me again.” Sam shook his head “No I don’t think I’d like that...I mean I’ll go on a date with you but….I doubt I’ll ever want you to stop talking to me all together.” 

Gabriel nodded “Good, now if I could just have…” Sam quickly grabbed a piece of paper and wrote his cellphone number on it and pushed it across the counter to Gabriel who stared at it. “I was going to ask you for your schedule so I could plan something for us.” Sam’s face went red. “Oh...I’m done at five tonight.” Gabriel nodded. “I’ll pick you up at your place at six thirty then.”

“I haven’t told you where I lived” Sam blinked and Gabriel smiled this time and turned. “I know where you live” He spoke as he walked out of the coffee shop. Sam couldn’t help the smile that filled his face and he twirled his hands going to his hair.He turned and looked at Jessica and blinked. “Oh Jess...oh shit Jess I’m sorry.”

“You could have just told me that you were into men Sam...I wouldn’t of been offended.” Sam opened his mouth to tell her that he wasn’t just into men but decided it’d just be better to go with it. Tell her that he was into women too and she’d demand to know why he didn’t like her. He didn’t quite know why he didn’t want to be close to her. He was just always afraid when he thought of it...like she’d turn to ashes in front of his eyes if he got to close...like she’d only get hurt or worse...burned.

“So what are you going to wear?” Jessica pulled Sam out of his trance and he blinked. “What?” Jessica smiled “What are you going to wear? IF I can’t love you I can at least help you find love...come on I”ll come over after work and help you get ready. Believe me I know what to do to you to make you look good. I’ve had my dreams.’

Sam turned to start to clean up when he blinked “What?” He looked back at her and she shook her head. “Nevermind”

At five when he was done he felt his stomach knott “Jessica I shouldn’t of said yes.” he muttered as they walked out of the shop together walking around to the back to their cars. “Come on you’ll have a blast, he looks like a nice guy.”

“He likes control..” He muttered and Jessica laughed “In bed?” Sam’s face went a brilliant red and he gasped “NO I meant in general god why does everything have to be about sex with you.” Jessica laughed “Two words Sam, your brother.” Sam rolled his eyes and sighed. “Yeah I guess you win.” Sam slipped into his car and started it, knowing Jessica was going to follow him home anyway….tonight Sam had a date...with Gabriel Novak.

Sam looked down at himself and shook his head, he had let Jessica dress him in a black button up shirt and a pair of jeans that were a bit tight. He ran his hands through his soft hair and he looked in the mirror before looking back at Jessica. “Come on Jess this isn’t me…” Jessica smirked and shook her head “Okay, take it off there’s only one more shirt I can think of.” Jessica disappeared back into his walk in closet and she reappeared in a blue plaid shirt and Sam blnked “Come on Jess this is a date.” Jessica groaned “You know what Winchester you are one picky sob.” Jessica returned this time with a maroon button up and Sam blinked “I...like that color” he smiled and let Jessica dress him one last time. 

When Sam heard the buzzer he heard Dean get up and Sam quickly ran from Jessica.”No! I’ll get it!” Sam pressed his thumb against the buzzer “Hello?”

“Hello Samuel it’s Gabriel” Sam blinked at the use of his full name and pressed the door button and turned and saw Jessica standing there her eyes a little dark. “Oh...um, this must be awkward if you want”

“Yeah…” Jessica moved around Dean and out of the apartment and Sam looked over at Dean. “How do I look?”

Dean laughed ‘Yeah uh, you look fine? I don’t know but just...watch yourself okay. He’s a bit of a high roller and sometimes he expects things.”

“How do you know?”

Dean shrugged “I’ve done my research...I think I know his type”

“You could be wrong” Sam sighed and then jumped when a knock came at the door. Dean smiled and grabbed his leather jacket. “You better hope I’m wrong then.” He whispered and opened the door smirking at Gabriel. “Home by midnight would ya” He winked joking and walked past Gabriel and Sam took in a breath and smiled once Dean was gone. “Uh hi…” he rubbed the back of his neck and nodded into his apartment. “Do you want to come in?”

“Actually I have a limo waiting..”

“A limo?”

“Yes my other car is in the shop” He joked and Sam laughed nervously and Gabriel raised an eyebrow at him. “Are you alright Samuel?”

“Where did Samuel come from?” He laughed nervously again “Sam’s fine you know” Gabriel’s jaw hardened and this made Sam’s heart leap in his throat. “Actually it’s quite a different relationship we have no and I believe using your full name would show you the respect you deserve.”

Sam nodded “Okay….that works” He stared at Gabriel before grabbing a jacket. “Where are we going anywhere?”

“I have a friend who’s opening a restaurant and he asked if I’d taste his food before he does his grand opening. He promised me his vip area as well so I thought why not.” he smiled “There will be a function of fifty in the main restaurant but we shouldn’t be bothered by any of it. Sam blinked and nodded, it only made sense someone like him who was always in the media wouldn’t want to be seen with Sam. Walking out of the apartment he locked it behind him and then made his way to the elevator. Pressing the button it dinged right away and opened up, slipping into the empty elevator he looked over at Gabriel who was staring at him from his far corner. Sam didn’t know how but somehow Gabriel’s eyes were darker, more alluring. It had made the very quick elevator ride extremely tempting.

[i]Come on Sam you just met the guy [/i]

Slipping into the limo it looked like a normal limo to him. He shuffled down the seat a little leaving a seat between him and Gabriel. “SO Samuel, have you always wanted to work in a hardware store?” Sam laughed “No….Not even in the slightest! I’ve always wanted to be a lawyer but getting a scholarship was impossible and I can’t afford the schooling. I’m in the process of trying to think of something else I can do.” 

“You should never allow money to control your dreams.”

“Tell that to the tuition people of every high ranked university in the country.”

“I might have friends who know of scholarships that you can apply for.”

Sam blinked and stared at Gabriel who looked extremely serious. “Oh..no no I couldn’t impose I mean I graduated highschool years ago I mean I’ve done some paralegals courses but...I’m too old to be getting back on that school train.”

“You are never too old for anything, you’ll learn that one day.” Gabriel let his eyes trail away from Sam and Sam felt himself shiver.


	5. My dinner with Mr. Novak

**Summary for the Chapter:**

> Sam gets a glimpse into the real personality of Gabe Novak over dinner.

The restaurant was located downtown not to far from Gabriel’s tower. It was a nice quiet italian place from the looks of it. Sam and Gabriel were lead to a back room that was copletely red and black. He suddenly felt a little weird seeing as his shirt was red. But then he noticed that Gabriel’s tie was also red, this was starting to become a bit much.

“If I didn’t know any better I’d say you planned this entire color scheme.” He looked over at Gabriel who smiled shortly and shrugged. “Just a coincidence I suppose” He walked around the booth they were given and then looked over at Sam quickly. Sam blinked “Do you believe in coincidences..” Gabriel finally sat down looking up at Sam as if they were doing the interview all over again. “No” Sam blinked and pulled off his jacket and sat down. “So, why this place.”

“I like privacy I told you”

“It’s so no one sees you on a date with me.”

Gabriel looked up at Sam quickly, his eyes narrowing a little and Sam blinked and wanted to become very small in his seat. “I’m sorry I -”

“Never presume to know how I feel about anything. I wanted us to have privacy because often times when I dine in public many people come up to me and often ask me for business advice…” Sam shifted in his seat “I’m sorry”

“Don’t...apologize Samuel it’s fine.” he looked up at Sam and straightened his tie a little when their server a short blond girl came in. “Hello, I’m Amy and I”ll be your server tonight.” Sam looked up at the girl and blinked, it was a strange coincidence that she was blond. It was like the man surrounded himself with blondes...but Sm wasn’t blond in the slightest. “Drinks?” Gabriel looked at the woman for a quick second before he took in a breath. “I have a bottle on hold, tell Dwayne I’m here he will give you what I want” The girl nodded and disappeared before Gabriel looked back at Samuel “So besides being a lawyer any other dreams? Desires?” Sam shrugged “Not really I mean I’m just …..I don’t know I’m just living life right now.” Gabriel nodded and then Amy walked back in with their bottle of wine and was about to pour it when Gabriel took it from her and she blinked “I’ll be back with the menu’s sir.” She whispered and disappeared. Sam shifted “Um I know this is me overstepping my boundaries here but she’s trying to do a good job couldn’t you cut her some slack.” Gabriel blinked and smiled “Sorry Samuel...I’ll be nicer” Sam raised an eyebrow and nodded “Thank you.” Sam went to open his mouth and blinked “I’ve just...I’ve done her job it isn’t easy and you can be kinda intimidating.” Gabriel looked up at Sam and Sam’s mouth went dry, it was like all the light in the room pooled in his eyes and Gabe blinked “Are you intimidated?” 

Sam quickly looked down at his empty plate.

The rest of the night was generic and bland Gabriel asked interview type questions and Sam answered and by the time they were half way into their entree when Sam sighed “Okay what did I do”

“Nothing? I’m sorry I don’t understand” Gabriel looked mildly interested.

Sam sighed “ When we first came in, you were...you commanded the entire room with your stature alone and now your acting like this is an interview for some magazine you couldn’t care less about. Did I offend you?” Gabriel folded his hands in his lap and looked up at Sam. “You asked me to be nicer and this is the only way I know how to.” Sam nodded and Gabriel reached across the table suddenly and looked at him. “If you can accept me as I am, I”m sure you’ll enjoy yourself so much more around me.” 

Sam wasn’t sure if it was the man’s hand touching his , or if it was the fact that Gabrie l was suddenly so close to him that made his stomach clench and he nodded “Okay, so be yourself then.” The words came out as barely a whisper and Gabriel nodded. “Are you enjoying your food?”

Sam shrugged “Um well -”

“Make sure you finish it Samuel” Gabriel’s attitude in a minute changed back. Sam smiled a little at the familiar attitude but at the same time he was unsure how to react he really was getting full but by the sound of Gabriel’s voice. “Can I get to go?” Gabriel shifted and pulled back his hand. “As you wish.” Sam nodded and shifted “Good then I’ll take it to go. Are we staying for dessert?” Gabriel quickly looked up at him and shook his head “I never have dessert on the first date. But perhaps we can talk about arranging another meeting.” Sam smirked and looked around. “Is something amusing?” Sam shrugged “You treat dates like business meetings, I’ll get used to it, it’s just kinda funny right now.” Gabriel nodded and Sam licked his lower lip. “I have a friend, Becky and she has this art exhibit that’s coming up and I thought maybe you’d like to come? I mean I wasn't thinking about it, I’m going and since you want to do another meeting perhaps that could be it? You’d be meeting my friends”

“Your brother again” Gabriel looked over at Sam who nodded ‘Uh yeah he’ll probably be there too.” Gabriel nodded “When is it?” Sam blinked “Um I believe it’s next Saturday” he nodded and that’s when Amy walked back in and Gabriel motioned for the woman to clear the table. “Come I’ll bring you home.” Sam blinked and pointed towards the plate Gabriel raised his hand and Sam watched Amy quickly grab it and hurry off. Gabriel walked around the table and grabbed Sam’s jacket and held it out for him. “Thanks” Sam had to lean over a little to slip into his jacket because of the height difference. The drive back home was about as intense as the drive there, Gabriel being so close, his knee inches from Sam’s. He had to shift his hips to try and keep himself from becoming aroused in the man’s presence. As the limo pulled up to Sam’s apartment he looked over and saw Gabriel looking at him. “So Saturday?” Gabriel suddenly pulled Sam close in a hungry way and placed his lips on Sam’s and that was enough for Sam to melt into the smaller man. His hands reached up to cup Gabriel’s face but he found the smaller man’s hands grabbed his quickly and the kiss was over. Sam breathed deep inhaling Gabriel’s scent and cataloguing it to memory. Gabriel cleared his throat. “Goodnight Samuel Winchester” Sam blinked and nodded reaching back for the door handle. “Goodnight Gabriel.” Sam quickly slipped out of the car and walked quickly to the apartment building.

When Sam walked into his apartment he saw Dean sitting at the kitchen table “Well?” Sam shook his head “Seriously you waited up for that?” Sam walked through the kitchen to his room and Dean laughed “Your mouth says no but your pants say yes?” Sam quickly looked down to see if he was still spotting an erection and Dean burst out laughing. “Oh my god you slut you fooled around with the man!” Sam blinked and walked into his room. “You can shut up now Dean.” He closed his door.


	6. Drinking away crossed wires

**Summary for the Chapter:**

> When Sam has a stressful week and calls Gabriel he's shocked at the man's response. His reaction caused Sam to go to Jessica's hosue for a few drinks, and a few regrets. [[Some light Sam / Jess ]]

Sam’s week was full of stressful commercial auditions, gossip filled coffee shop shifts and then there was home. Ever since Sam’s date with Gabriel Novak Dean had been different, his personality it was like something changed in him. Thursday night after a particularly horrible audition for a hiv medication commercial that he was a little too worried he got he walked into his brother dancing around the kitchen with a bottle of whiskey in his hands. “What the hell are you doing” Sam froze and Dean looked over at Sam and put his finger to his lips “Shush! Shut your mouth will ya I’ve got a ...chick over.” Dean nodded towards the door and Sam slowly looked over to the room where he saw just red hair. He looked back at Dean and the man smirked and ran up to him. 

“Look she’s staying the night so...wear the noise cancelling headphones will ya?”

Sam shook his head “I’ll just go stay the night at Jessica’s” Dean smirked and smacked his chest “Good, keep the playing field open.” Sam shook his head and walked into his room and slammed the door shut before he grabbed his cellphone and sighed as he started to scroll through the contacts.

He froze when his thumb hovered over Gabriel’s cellphone number, he knew that he wasn’t supposed to meet the man until Saturday but he wondered if the man would be interested in having an impromptu cup of coffee. Tapping the man’s information with his thumb he put the phone to his ear and jumped backwards onto the bed. He heard the phone ring several times before Gabriel answered it slightly out of breath. “Samuel” Sam smiled, almost getting used to and enjoying when Gabriel called h that. ‘Gabriel.” Sam chimed back and took in a breath. “I have just had the wo-”

“What’s wrong Samuel? Are you okay?’ Gabriel quickly spoke and Sam blinked “Uh, ea I’m fine I was wondering if you wanted to go out for a cup of coffee” Sam could hear Gabe’s jaw harden “I’m busy” Then the phone hung up and Sam pulled back the phone. “Well okay then…..” Sam sat up and that’s when he could hear the woman Dean had brought home moan and he shook his head. 

“I’m out” He grabbed his noise cancelling headphones and put them on as he grabbed his cellphone texting Jessica letting her know he was coming over.

\-----------------

“Was it that bad?” Jessica laughed as she opened the door, pushing some blond hair out of her face she looked up at Sam who sighed and held up his noise cancelling headphones like it was a participation badge at track and field day. “I didn’t take these off until I hit the elevator.” Jessica shook her head and started to laugh “Seriously though I thought for a while there he was going after men.” She moved out of the way and Sam walked in and threw his bag on her couch and then slowly turned around. “Yeah about that” Jessica sighed and walked past him. “Sam look it’s...it’s fine if you don’t want me anymore. If this Gabriel guy is what’s doing it for you these days who am I to step in the way?” Sam smirked looking at her in mild disbelief “I’m kinda surprised your taking it so well. “ Sam pulled off his jacket and threw it on the couch and suddenly Jessica was beside him with a glass of wine. “Want a drink?” Sam scrunched up his nose and Jessica laughed and handed him a beer. “You know for someone who’s digging guys your far to -” Sam pointed at her “No stereotypes Jessica, look I can’t explain it I just…” He shrugged and took a drink of his beer and sat down.

Jessica sat down beside him and grabbed her remote for the t.v. and leaned against the taller man. “What shall we watch tonight?” Sam looked down at Jessica and looked around for a moment. His mind started to wander to the conversation he had with Gabriel before he came over. “I actually don’t know if me and Gabriel are going to work out.” Sam sighed and Jessica looked up at him. “Oh you know I haven’t seen that one is it on ppv?” Sam looked down at Jessica and shook his head “you know if I wanted that kind of response I would have spoken to Dean about this.” Jessica laughed “Oh yeah, while he’s got madam redhead bent over a table? Perfect conversation, now...look why do you think it’s not going to work out?” Sam shifted and took a drink of his beer and shifted his body so he was looking at her.

“I called him tonight, you know just to see if he wanted a cup of coffee, and just hang out. But then he just blew me off and hung up on me….he didn’t even tell me what was going on he was doing he just said ‘I’m busy’ and hung up.” Jessica blinked “What did it sound like he was doing?” Sam sighed and started to play with the label of the beer “He was out of breath.” Jessica sighed and finished her cup of wine and climbed up and hugged Sam “Sorry love.” Sam nodded “I figured as much but, I mean he was really nice to me he took me out for dinner. We bumped heads a little but it was...on the way home it felt good, it felt really good.” Sam finished off his beer and sighed. Jessica took the beer and stood up “I’m going for a refill you want to join me?” Sam stood up and Jessica laughed “I just meant do you want another” Sam nodded ‘Yeah but I’ll come into the kitchen with you”

Jessica lead the way into a small purple walled kitchen. Sam blinked “When did you paint the walls purple?” Jessica smiled “Ah yes this is my fuck you to my landlord.” Sam walked over and pulled open the door to her yellowish fridge and saw a bottle of gin “Oh Gin”

Jessica quickly eyed Sam and shook her head “Are you sure Sam? You remember the last time we drank gin” Sam smirked “No that’s the point” He grabbed the bottle and walked across her kitchen in two short strides and grabbed two shot glasses “Just two shots..” Jessica moaned “Can’t we just drink it with juice?” Sam shook his head “Nope….Nope I’m “ Sam poured two shots and Jessica went to grab one and Sam took both and swallowed them. “Well damn Sammy…..share much?” 

Sam looked over at Jessica and sighed “What...what about me doesn’t work?” Jessica reached forward and took a shot and watched as Sam grabbed the shot and swallowed it quickly. Jessica stared at the shot and swallowed it and shook her head “Nope...we’re not doing this Sam”Jessica took the bottle from the taller man and put it back in the fridge and turned back to Sam standing above her. “What is it Jessica? Is it my kisses” Jessica opened her mouth and blinked “Sam we didn’t really…..” Jessica wasn’t able to finish her sentence when Sam was suddenly on her his mouth kissing hers clumsily his hands reaching out for her shirt. Jesssica pulled back and blinked “Sam you don’t want this.”

“I need to know I’m good for someone Jess, you still want me don’t you?” Jessica shook her head and laughed “I can’t believe I’m the one saying this, but Sam your drunk and I just couldn’t..” Sam smiled “So drink with me” He went to move to the fridge and Jessica sighed “It wouldn’t be real.” Sam looked back at her and his face went serious. “Jess don’t think for a second that how I felt about you wasn’t real” Jess crossed her arms over her chest “Oh you felt for me?” Sam blinked “Look I know I didn’t “ “Sam I asked you out on a bunch of dates and you turned me down...felt something for me?” Sam opened his mouth “We went out a few times” Jessica laughed “Sam, there’s nothing you could do that would make me think you wanted me.”

Sam smiled “Challenge accepted” Jessica went to move backwards before the younger Winchester had her up in his arms and carried her back to the bedroom. Dropping her lightly onto the bed Sam leaned over her kissing her softly. In the back of his mind he wasn’t sure if he was doing this to prove to himself that he could, or because Gabriel lead him on. But as he pulled off Jessica’s shirt he realize he might have been doing it for the second reason. Kissing down the woman’s neck a feeling started to bubble in his stomach and it didn’t feel like regret. Taking one of her nipples into his mouth his tongue ran over it and when Jessica moaned out Sam smiled to himself. That feeling growing in his stomach as he moved down her body, his fingers already working on her pants as his lips reached her stomach.

“Sam” He heard a small voice from beneath him and he looked up his head swimming as he stared up at Jessica. “Yea Jess..” he ran his fingers under the waistband of her pants and she shivered and he smirked and kissed her stomach again as he slipped his hands under her pants and underwear and with one swift motion pulled them off.

“Sam” this time it was a moan and Sam smirked and looked up “Are you sure about this?” Jessica whispered and Sam paused. That’s when that odd sensation in his stomach rose and he suddenly ran from the girl’s bed and into the bathroom his head diving into the woman’s toilet as he emptied his stomach.

Jessica sighed and shook her head. “My luck...’ Jessica grabbed her house coat and walked out into her kitchen and grabbed her cellphone dialling Dean’s number “Dean” Jess didn’t give him much time to answer “Come get your brother he’s sick and drunk…” Jessica hung up and ran her hands over her face. “I need a cold shower”


	7. A simple misunderstanding

**Summary for the Chapter:**

> Hey everyone! First off sorry for not posting in a while I ended up getting sick and then the holidays! I"ll be making up for it by posting two or three chapters in the next couple of days!
> 
> Sam decides that maybe Gabriel isn't the man for him and tries to go back to life as he knew it. But Gabriel is standing there in the way to pull the man back.

Sam after suffering the worst hangover he had in the past year decided that he was going to put Gabriel Novak on the back burner. If the man really was just trying to get into his pants well he didn’t want to have anything to do with it, plus he had to focus on his possible acting career.

Sam sat at the table in the apartment and blinked when he saw an envelope on the table with his name on it from a local acting college. “Uh Dean? When did this letter come in?” Dean popped his head out of the bathroom his tooth brush in his mouth and he blinked. “Oh I found it in the middle of my magazine, must have been jammed in there in the mail.” Sam blinked and opened it and stood up. “Dean this is an acceptance letter to the college in the city! My last day to hand in my first half of tuition is today!” Sam slumped back down into his chair and shook his head “I don’t even have half of that” Dean blinked “Sorry Sammy, sometimes I don’t go through my magazines if I don’t need to.” Sam rubbed his face. “You always need to….it’s..it’s fine I”m not mad at you. I got accepted and that’s the main thing, I guess I can just reapply in the spring.” Sam sighed and looked up at the clock. “I’m gonna go to work a little early...I’ll be home later.”

Dean shrugged and went back into the bathroom and Sam rubbed his face before he grabbed his jacket and went to go to work. When he opened the door of his apartment Gabriel was standing there. Sam looked over the man and almost moaned. The man stood straight, wearing a black suit with a black undershirt and a red tie, god he could think of a million things to do with that tie. Suddenly he blinked crossing his arms. “I’m sorry do you need something?” Gabriel gave the man a shocked and hurt look. “Is that how you greet people now?” Sam’s mouth dropped and he walked out into the hall and closed the door behind him, his brother didn’t need to hear what he was about to say.

“Look, the other night when I called you..you were rude to me so I really don’t -”

“You didn’t tell me you were going to call, I was in a meeting and I prefer to keep my personal life and my business life separate.”

“For a business meeting you sounded pretty winded.” 

Gabriel straightened his tight. “Samuel wouldn’t you prefer that we talk about this in your home?” Sam shook his head “No I wouldn’t prefer if we talk about this in my home! I just wanted to talk to you and you were rude okay? I’m not here to be ...toyed with okay. If your trying to impress me with your money colour me impressed but...that doesn’t mean you can treat me like that.”

Gabriel nodded ‘Your implying that you believe that I’ve been trying to...woo you with my money in hopes to sleep with you.” 

Sam suddenly felt like an asshole. “Um…”

Gabriel nodded again. “Sam” Gabriel’s short for of Sam’s name made the man blink for a second. “If I were simply trying to get laid...I know a lot of women, a lot, that would do it for half the price of our meal the other night. I also know a lot of women who would do far more for double. So I want to make it very clear that nothing I am doing here is simply for sex? Do we understand each other now?”

Sam nodded “Yes”

“Good, now when I’m in a meeting, and I hang up quickly it’s simply because I’m in a meeting, or I am busy. Like I said when we first met, I am all about total and complete control and that means scheduling my days almost down to the second if I can help it.”

Sam laughed and walked past him. “So somewhere in your day book you wrote down ‘make up with Sam’ in it?” Sam headed towards the door that lead to the stairwell and Gabriel put his hands in his pockets. “Making up implies that we are in a relationship. Are we in a relationship Samuel?” Sam froze his hands on the push bar of the door and he looked back over at Gabriel. Was the man asking for some sort of clarification on their relationship, and was Sam ready to put a label on their relationship.

“What would it mean if it were?”

“Well if we are in fact in a relationship” Gabriel started and looked over at the man slowly turning his body and walking towards him. “Then I would in fact need to make up with you, as I’ve wronged you somehow. But if we’re in a relationship Sam, there is a lot of things we have to talk about. There are certain things about me you have to know and understand. I’m not like other people Sam and being in a relationship with me isn’t as simple as you might think.”

 

Sam laughed “What are you going to do make me sign a clause for all your dirty little secrets so I don’t sell you out to the media?”

Gabriel’s eyes narrowed and Sam blinked “Holy shit”

Gabriel let out a breath, “You are on your way to work, how about we talk about this tomorrow night over dinner?” Sam nodded “Oh...Yeah sure I’ll switch my shift no problem.” Gabriel looked over at Sam. “Sam, if you come to dinner with me , please have an open mind for what I’ll be discussing with you...like I said being in a relationship with me is no simple matter.”

Sam nodded and pushed open the door and Gabriel blinked “Why do you walk down the stairs?” Sam shrugged “It’s cheaper than going to a gym?” 

Gabriel nodded “I heard you talking about school- “

Sam blinked “How long were you standing in front of my door”

Gabriel smiled “I’ll talk to you tomorrow Sam” Gabriel turned and headed towards the elevators while Sam walked into the staircase. A large smile covered his face as he started to take the stairs two at a time as he bounced down to the street. When he pushed out he saw Gabriel’s car pull away and he smirked and stuffed his hands in his pockets and started to walk the opposite way towards the coffee shop.


	8. The contract

**Summary for the Chapter:**

> Gabriel brings Sam over for dinner and to show him the contract that he must sign in order for the relationship to start.

Sam stared at himself in the mirror as he tried to tame his long hair. He shook his head and sighed “Dean do you think I need a hair cut?” He popped his head out of the bathroom to look at his brother who was sitting at the kitchen table with a grocery store flyer in front of him. “Hmmm?” He grabbed a pair of scissors and suddenly clipped out a coupon and Sam blinked “Are you couponing?” Sam walked out of the bathroom and Dean looked up “Well if we’ve gotta save money for your schooling in the spring I figured why the hell not cut out a couple of coupons, I mean your the one who does the shopping anyway” Dean smirked and Sam shook his head “Dean, hair cut?” Sam motioned towards his hair again and Dean looked up and shrugged “How the hell am I supposed to know? Your hair’s always been long..I’m afraid if you cut it, your hair will become enraged and kill us in our sleep! I’d hate to have to do an exorcism on your hair.”

Sam laughed “You don’t know how to do one “ Dean shrugged “I’m sure I could figure it out...why do you care what you look like tonight anyway?” Sam walked back into the bathroom and sighed. “Gabriel’s taking me out for dinner.” Dean smirked and stood up “So that’s date number two….sounds kinda serious” Dean wiggled his eyebrows and Sam shook his head “You know, for the most dude like guy I know your pretty cool about this.” Dean blinked “Dude like guy? Oh god never say that again, and look man...if you wanna go hunting for chicks sure I’m by your side and if you wanna go hunting for dudes...well just point me towards...look you know your my brother. I’m gonna love you either way I really don’t have a choice in the matter!

Sam smirked “Thanks Dean.”

“But Sam” Sam popped his head back out of the bathroom and Dean smiled “Change, okay if your going out with this guy ...dark jeans and a dark t-shirt man, have I not taught you anything.” Sam smiled “Actually I’m gonna change into dress pants...I don’t know where he’s taking me so.” Dean laughed “Oh right you got the one I should have had, I gave you that one just remember that.”

“Yeah I don’t think you and Gabe would have worked out” Sam gave up with his hair and left the bathroom walking towards his bedroom. “Oh yeah and why’s that?” Dean walked back to the kitchen table and sat down clipping out another coupon. Sam looked back before he dodged into his room. “Because Gabriel has class.” Dean blinked and shook his head “Oh kid, I’mma beat you when your not looking.”

To avoid awkward conversation with Dean Sam waited for Gabriel downstairs in the lobby, when he saw Gabriel’s car pull up he skipped out into the street and saw Gabriel staring at him with an odd look. “What?” Gabriel shook his head “Nothing, I just thought a proper date should start with me picking you up from your home, not from the lobby of your home.” Sam blinked “oh sorry, Dean’s in a wierd mood so...is this okay? You didn’t tell me where we were going yesterday so.”

Gabriel nodded “It’s fine but we’re actually going to be having dinner at my house tonight if you don’t mind.’” Sam walked up and slipped into the passenger seat and Gabriel climbed in and that’s when Sam realized how dressed up he was in comparison to Gabe. The man beside him wore a black t-shirt and a pair of dark blue jeans, cowboy boots on his feet.

“Oh I’m dressed up I ….I should have asked” Sam muttered and Gabriel shook his head “No you look fine.” The drive to Gabriel’s was long and silent.Gabriel would ask short questions and Sam would return in kind, they spoke about work, or well Sam spoke about work and Gabriel listened. “I’m just going to save up what I can and hopefully go to school in the spring.”

“What for?” Gabriel looked over and Sam smiled “Acting” Gabriel smiled and the rest of the car ride was silence.  
When Sam got out of the car in the underground parking lot he stretched and Gabriel smiled “Not used to car rides Samuel?” Sam looked over at Gabe and shook his head “Nope, I’m too used to it actually my brother drives a 67 Impala.” Gabriel made a face “Sounds like a beautiful machine if it wasn’t horrible for the environment.” Sam frowned and Gabriel smiled and walked over to a large silver elevator and pressed his thumb against a silver plate and it opened up.

“Come on in Sam” Sam followed the man into the elevator.

Oh the elevator, it was Sam worst friend as he had too many dreams about things he could do to Gabriel. He looked over at the man and felt his body growing warm and looked away a soft music box version of Wayward Son playing over the speaker. When it opened Sam raised an eyebrow. “Are we at your office?”

Gabriel laughed “No I just so happen to have very simple tastes.” Sam walked in and saw the maroon halls that lead to a white door. He walked behind Gabriel and the man opened his door and walked in. Sam followed behind and his jaw dropped and he looked around the house. They walked into a large open room with high ceilings and dark red and brown walls. He saw a large screen t.v and a set of white couches to his left and to his right he could see a door that lead to what looked like an office. Looking back at Gabriel the man smiled and nodded his head down a hallway. Sam followed Gabriel into a very large kitchen with a large white table, the room had a pair of double doors that lead to a balcony. Granite counters, the entire room looked like something from a magazine. 

“Wow Gabriel your house is fantastic.” Gabriel smiled “It took me a long time to finally be happy with this place, like I said”

“You like control” Sam nodded and Gabriel smiled “Yes..” Gabriel walked behind the counter and took in a breath. “I don’t have a maid, or a cook, I prefer to do everything myself because then I know what’s going on with my food and no one is listening to my business calls. I have a chef that comes in once a week and prepares meals for me when I’m most busy and occasionally will teach me new techniques I have yet to master. I have a cleaning lady that comes in every Sunday, her name is Anna.” 

Sam sat down at one of the bar stools at the kitchen nook and Gabriel pulled out a large bottle of wine and two glasses from under the nook and put them on top of the counter. Pouring wine into both he gave Sam’s hand a soft smack when he reached out for one before he pointed at him. “I’m not tryin to get you drunk...we’ll eat with our wine.”

Sam smiled “I have eaten today you know that right.” Gabriel nodded “I believe you, but I want to see you eat first..” he walked over to the fridge and pulled out a tray of chocolate covered strawberries. “One thing you should know about me, is that I have a never ending sweet tooth. Because of this I...have a very extensive physical schedule.” Sam raised an eyebrow and Gabriel pushed the platter between the two and took a strawberry and held it out for Sam to bite. Sam licked his lips and raised an eyebrow before giving in and leaned forward a little, his eyes flicking over to the beautiful hazeled eyed man who held it and bit the strawberry. Pulling back he blinked “Wow those are good” He put his hand in front of his mouth so the man couldn’t see him eating with his mouth full.

“When you called me the other night I was boxing, I wasn’t in a meeting, but I really don’t want people knowing I box. So I rarely tell people.” Sam shook his head “Why?” Gabriel sighed. “Sam I made my first million when I was twenty three years old. I’ve been making millions since and ever since I made my first million everyone wants to get into my life. Simple details of my life, such as my gym routine are precious because I don’t feel like people snooping into my life. Understand?” Gabriel took a strawberry and ate it before he looked over at Sam. 

Sam could feel a shiver run down his spine, the man’s gaze alone was enough to have him writhing on the floor if he told him to.

“Okay, so you have a lot of secrets….because you don’t want people to be able to follow you.” Gabriel nodded “That is one of the reasons yes. But first…” Gabriel walked back to his fridge and pulled a casserole dish from the fridge and put it into the over and pressed a button. He then pointed at the seat Sam was sitting. “Stay” Sam blinked “Okay..”

Sam reached for the wine bottle and he could hear Gabriel’s voice echoing down the hall “Not yet Samuel” he frowned and grabbed another strawberry instead. Dessert before dinner, this man really did have a sweet tooth. With Gabriel returned he had a black duotang in his hand and he put it down between them. “This is a legal agreement, if we decide to pursue a relationship I need you to read this and sign it.” Sam held out his hand. “Give me a pen.” Gabriel frowned. “Sam I need you to read it.”

Sam sighed and pulled it towards him and opened it and his eyes went wide. The letters were font 9 at best and there was six pages to read. “What the hell is this?” Sam looked up at Gabriel frowned a little. “When you’re done reading, dinner will be ready.” Sam leaned forward his chin in his palm as he started to read. Some of what was on the pages was normal if you were getting a job that had a lot of publicity. But then there were some things that were just plain weird. “Why do I have to get a physical done every three months I’m with you?” Gabriel had been reading a magazine on the other side of the nook, he looked up and blinked. “I need you to always be in peak physical condition.” Sam nodded “Is that why the gym membership is included?” Gabriel looked down at his magazine. “You look great Sam, I want to keep you that way.”

Sam shook his head and continued to read, some of the points in the contract were beyond bizarre but the young Winchester couldn’t be bothered to believe that all of this was true. When it came to the legalities of keeping away from reporters and not telling anyone where Gabriel lived save one family member he could tell it was almost like getting into a relationship with a movie star or something.

Sam twirled the pen in his hands as he finished reading, as he looked up there was a soft ding and Gabriel stood up “Dinner is ready, are you done reading?” Sam nodded “Yup, and that contract just reminded me why I didn’t become a lawyer.” He laughed and Gabriel frowned “You were going to become a lawyer?” Sam sighed “My...parents wanted okay my dad wanted me to become a lawyer, he was a lawyer...kinda the family business.” Sam licked his lips and laughed. “This is all a joke right? I mean “ he saw Gabriel’s face stiff and Sam cleared his throat. “It’s just there are some things in here that are down right weird Gabe, I mean..okay this” He flipped through a few pages and pointed a point. “ You want me to keep myself regularly groomed? I do that anyway.” Gabriel nodded “Yes but I will provide the services, I will provide where you get your haircut...where you will get waxed.” 

Sam laughed “Yeah about that, I like my body the way it is…” Gabriel nodded and licked his teeth. “You may...one day decide that a wax is...a useful thing.” Sam raised an eyebrow and took in a breath. “Okay look, I’m going to sign this but Gabriel...If you want me you want me for me, all these things in here...it sounds like you want me to be someone else.”

Gabriel rubbed his forehead “Sam, sometimes I have to go to parties, sometimes I have to be in the eye of the people and for those occasions, I need you to look like someone you’re not.” Sam frowned a little “Oh….” the pen wavered in his hand and he shook his head and signed it. “Whatever I’ll give it a shot.” Gabriel sighed “There’s a seventy two hour period where..if you want you can get out of the contract without any hassle.” Sam blinked “I’m sorry what?” Gabriel looked over at the man. “I’m saying that I’ll give you a few days to think about it, and decide if this is for you or not. I have a very intense life Sam.” 

Sam smiled and pushed the contract towards Gabriel “Consider me signed up.”


	9. A long morning

**Summary for the Chapter:**

> While trying to decide how Sam wants to go about dealing with Gabriel's strange request to come to the office an unexpected guest shows up at the Winchester apartment.

“So are you going to go to the office then Sammy?” Sam looked up at his brother who was smirking a little too much at his brother. “Dean...I don’t know” Dean smiled and put a plate of toast, bacon and scrambled eggs in front of the man. “Dean it isn’t that simple” Dean sat down with his own plate and blinked opening his mouth before he shoveled food into it and chewed, his mouth still open a little. “Let me get this straight” He swallowed his mouthful and drank some orange juice. “A wealthy, well groomed, decent looking -” “Hey” Sam looked up and Dean held up his hands and shoveled more food into his mouth. “Look, whatever maybe he’s just not my type anymore.”

Sam sighed “ He isn’t your type because you found out he likes me” Dean shook his head “Look I just don’t see the problem if you let him...give you stuff.”

“I’m not a whore Dean” Sam muttered and that’s when there was a knock at the door Dean quickly shoveled some more food into his mouth and pointed at his brother to motion for him to stay sitting down. Dean stood up and walked across the room and opened the door to see a man, slightly shorter than himself standing there. Dean smiled after swallowing his food and leaned against the door frame and eyed the man. “How can I help you?” The man was a tall drink of water, dark brown hair, crystal blue eyes and he looked so awkward standing there.

“I’m here for Sammuel” Dean laughed suddenly. “I’m sleeping right? Because there’s no way that this is happening...what’s your name?”

The man twisted his fingers “Castiel Novak” Dean blinked “Like Gabriel Novak?” Castiel looked around the hall “I am at the right address right?” Dean smirked “Oh yeah you are, I’m Dean Winchester I’m Sam’s older brother” he nodded into the house “Sam’s just eating breakfast”

Sam, once he heard his name quickly wiped his mouth and ran over to the door and saw the shorter man standing there “Hey I’m Sam, your Gabe’s brother?” Castiel nodded “Yes, he asked me to come pick you up. But by the look on your face, and the fact that you're eating breakfast I’ guess he didn’t ask or tell you I was coming.”

Sam shook his head and Dean perked up quickly “Hey why don’t you come in? I have extra’s if you're hungry” Castiel looked at Dean and blinked “I...I’m not very hungry but I can not leave without Sam so I suppose” He walked into the house and Dean almost squealed in delight. Walking into the apartment he walked over and grabbed a plate and started to get it ready with food. Sam blinked “Wait what if I didn’t want to go with you?” Castiel followed Dean to the table and sat down. When he sat down he looked over at Sam and blinked “I’m sorry do you not want to come?” 

Sam took his place back at the table and started to poke at his food a little “I hadn’t made up my mind”  
Dean saw Castiel look really uncomfortable and he shot Sam a look “He’s going he just wants to eat breakfast first.” Sam looked over at Dean who gave him a ‘go along with it bitch’ look and he sighed. “Jerk” Dean eyed the man “Bitch.” Castiel shifted in his seat and grabbed a fork to start to eat and then froze. “Did I interupt something?”

Dean laughed “No that’s just how we talk.” And so the three of them sat in awkward silence for a few moments only the sounds of utensils scraping plates were heard. Dean looked between Castiel and Sam and cleared his throat. “So Castiel that’s a ….really interesting name. It sounds almost -” “Angelic” Sam finished Dean’s sentence and the man shot his younger brother a look before he looked back at Castiel. “Do you have a nickname?” Castiel swallowed the food in his mouth and started to twirl the fork around in his fingers trying to think of an answer. “No, but I guess you can call me Cas, some of my brother’s call me Cas.”

“Some of your brothers?” Dean put his elbows on the table and looked over at the man placing his head in his palms. Sam groaned and quickly finished his plate and put it in the sink. “Dean don’t you have work to do? Castiel - Cas are you ready to go?” Castiel had opened his mouth to respond to Dean but when Sam quickly moved he stood up “Yes of course, “ he reached forward for his plate and Dean shook his head “Don’t worry about that I’ll get to it before I go to work. Unlike my brother here I wake up with plenty of time to do things.” Castiel nodded at Dean and then followed Sam out of the apartment. “I really need to have a talk with Gabriel.” Sam muttered and Cas looked over at the man. “He thought it would be more effective this way. Not to mention the route I take brings us to the hospital anyway.” Sam quickly jumped “Wait is Gabriel in the hospital?” Castiel quickly shook his head “Gabriel didn’t tell you anything did he?” Cas growled and pulled out his cellphone as he pushed open the fire escape to take the stairs down. He held the phone to his ear and then muttered something in a language that he didn’t understand. “Talk to your boyfriend then!” Sam heard Castiel hiss as they walked out onto the street and Sam saw Cas walk to a large SUV.

“Hello?” He took the younger Novak’s cellphone and heard muttering on the other end and then a throat being cleared. “Sam? Yes I see that Cas got you on time.”

“Yeah I’m confused I thought you just wanted me to come down to pick up some things.” Sam climbed into the car and put on his seatbelt and gave Cas a quick smile before he twisted his body so his face was towards the window. “I don’t get this, are you at the hospital?” He heard Gabriel sigh and frowned “No Sam, I”m fine, and yes I only have ...something to give you but first I need you to see my sister Anna I got a few strings pulled and I just need you to be tested.” Sam quickly pulled the phone away from his ear “Stop the car” he looked at Castiel who started to look frantically to his mirrors to find a chance to pull over.”Is something wrong.” Sam shook his head

“Gabriel all you had to do was ask, I’m clean I get myself checked regularly now -”

 

“Sam stop, please, I know that you get yourself checked, this is something that has to be done , please understand.”

“No, your...your starting to freak me out are you sick?”

Gabriel laughed “No, look please just stay in the car I promise you’ll , you’ll be happy in the end.” Sam growled and hung up the phone and looked over at Cas “I might kill your brother.” Cas smiled, and Sam blinked when he realized that Cas didn’t look that much like Gabe until he smiled “Get in line “ the dark haired man laughed and started to drive again.

“So...who’s Anna?”

“Oh she’s our sister?”

Sam blinked “How many are you?” Cas sighed “That’s a hard question to answer, our father he liked to um...he liked women.” Sam nodded “That explains that.”

Cas looked back at the road “Hm?” He gave Sam a quick side glance before looking back at the road. “Well you guys don’t look a hundred percent related.” Cas laughed “Well that makes a lot of sense seeing as Gabriel is the one kid that our father questions most of the time.” 

The rest of the car ride was filled with interesting tidbits about the brilliant golden hued haired millionaire. Childhood stories from the younger brother who, as it seemed, was more comfortable in the car than he was in the kitchen with Dean. When they got to the hospital Cas nodded towards the building. “I promise Anna is a whole lot nicer than Gabe.” 

Walking into the hospital Sam looked around as nurses all gave Cas smiles, was Castiel like his father? A lover of all sorts of women? Sam kept the question to himself as he followed the man down twisting hallways and ended up in a lobby full of men and women who looked rather normal for the most part. Cas gave Sam a sharp look “Manner’s Winchester” the man spoke and Sam’s eyebrows raised. Shaking his head he kept his eyes down as he followed Cas into a small room. 

“That was rude” Sam muttered to Cas and Cas blinked “Excuse me? Some of those people have been waiting for weeks for their test results and you’re going to get it instantly….don’t let Gabriel spoil you.” Sam shifted and before he could retort back to the Novak the door opened and a short redhead walked into the room and smiled.

“Hey Sam sorry for keeping you waiting, I’m Anna..” She quickly pushed Sam onto the bed in the room and looked the man open before she pulled open a small test kit beside the man. “Open your mouth” Sam blinked and didn’t even get a chance to speak and opened his mouth. He made an odd gagging noise as Anna swabbed his mouth and sighed when he was relieved with a cup of water.

“Don’t be such a baby. I hope you don’t mind needles” Sam swallowed the room temperature water and shook his head “No I’m fine.” Anna smiled and flipped over Sam’s right arm and smacked the inside of his elbow and once she found a vein she quickly got a small blood sample and smacked the man’s arm once she put a band aid on it. “Right Gabriel will have your results by the time you get to the office.” Anna nodded towards the door “Off you go I have patients to see.” Sam blinked and opened his mouth but before he could say anything Castiel grabbed his arm and pulled “Come on Sam” 

Sam looked over at Cas and shook his head “What is it with your family?” Cas looked back confused “What do you mean? What’s wrong with us?” Sam sighed. There was nothing wrong with them, he just found it odd how the entire family for the most part was bending to Gabriel’s wishes. Did the man really have that much power over his siblings? Unlike the trip to the hospital the trip to the office was a quiet one. In fact Sam made a point to keep his mouth shut until he was standing in the middle of the lobby of Gabriel’s office. Castiel had finally let him be by himself and the man had time to think. What the hell was he doing? This guy was going to be giving him something and just rushed him through an HIV test.

“Sam?” Sam turned and saw Gabriel standing there “Thanks for coming, come in” He nodded towards the office and Sam shook his head “Look we need to talk , I think this is a little too -” Gabe grabbed the man’s hand. “Come on Sam...we’ll talk in the office.” He pulled the taller Winchester into the office and Sam shook his head and once they were in Gabriel’s office he pulled his hand away from him. “Look, Gabriel I appreicate the rushed test but ...you could have just trusted me.” Gabriel sighed “Look, it’s not that I don’t trust you, I don’t trust myself...I had Anna come over this morning and test me before her shift started at the hospital.” Gabriel frowned “I just wanted to make sure we were both safe.” He smiled.

“Don’t you want to know what your results were?” Sam shook his head “I told you I’m clean….sure what are my results”

Gabriel’s face went serious very suddenly and Sam blinked “Wait what the fuck?”

“Your fine Sam..” Gabriel smiled a little and Sam sighed “Don’t do that to me that wasn’t fair...so why am I here?”

Gabriel’s smile suddenly got bigger and Sam was afraid for the answer.


	10. A few interesting offers

**Summary for the Chapter:**

> Sam finds out the main reason why he was brought to the office.

Gabriel shook his head and held out a large brown envelope in front of him and smirked “I thought I’d help out a little bit” Sam looked at him and took the envelope and opened it and blinked staring down at the papers he pulled out of the envelope. “This is an acceptance letter to the program I was ...going to apply for in the spring...but how did you?” Gabriel shrugged his shoulders. “I have a friend in admittance and when I find something worth investing in...I do” Sam suddenly realized what the man said and shook his head “Gabriel I can’t accept this, you’re paying for my schooling and according to this I start in two weeks. I mean..” Sam took in a breath and let it out. “I have already made your schedule for you, you can still work and have time with your brother...and you don’t have to share the apartment with Dean anymore.” 

Sam took in a breath and let it out “What are you saying? Did you get me a residence package too?” Sam started to go through the papers and Gabriel put his hands in his pockets. “No, the school is only fifteen minutes from my home...you can live with me.” Sam dropped the papers and looked over at Gabriel and shook his head “No...I’m sorry Gabriel but, I can’t accept this. You don’t know me, not really, and what do I know about you?” Sam motioned to Gabriel and let his hand fall and turned to the office door and Gabriel crossed his arms. “What do you think I’m trying to do Sam? I’m not asking you to marry me, I’m just offering my house for quick transportation.” Sam looked over his shoulder at Gabe who looked hurt, but also upset that Sam thought he was trying to buy the man. “I’ll know your schedule, I’ll know when you to pick you up, how late you can stay up andd I’ll be able to help you with a job too if the shop can’t work around your school hours.”

“See this feels like some sort of contract that I’m just not prepared to sign.”

“It’s not a contract, you don’t have to live with me it’s just an offer…” 

Sam took in a breath, “How about we start-” Sam bent over and started to pick up all the papers that he dropped and Gabriel knelt down and looked at him. “How about we start?” He raised an eyebrow and handed Sam the papers and Sam took them. 

“With a night over...I didn’t exactly stay the night last night.”

Gabriel stared at him. “Are you ready to spend the night at my house?” Gabriel asked, his voice low and husky. He wasn’t trying to be seductive he was just trying to keep his voice low. He didn’t want to force Sam to live with him and he wanted the man to know that, but he did want Sam to be his. He wanted to own Sam and he wanted no one else to look at him for any reason. Sam stared at him and he blinked “I don’t know, why don’t you call me tonight...I have a shift that starts soon.”

Gabriel nodded “Okay, I will

\------

Sam took in a breath as he put on his apron and took in a breath and let it out and saw Jessica walk up to him, perfect just the person he didn’t need to talk to. “You look stressed you okay?” the blond girl leaned against the coffee machine beside Sam and he looked at Jessica and his jaw tightened as he looked away. “Gabriel is offering to pay for me to go to the Acting program that starts in two weeks..and he….he said I can stay with him while I’m going to school.” Jessica took in a breath and took a step back, she looked upset, and who wouldn’t be...the man came in and picked up her ex and bought him.

“Wow, looks like you hit the jackpot there Winchester” She stood up and stiffened and Sam looked over at her “It’s not like that…” Sam walked out of the back kitchen and started his shift. For two hours he dealt with the breakfast rush and it wasn’t until the last of the lunch guests left the shop that he finally had time to think about what Gabriel had offered him.

“If you take it, I’m using your room for orgies...I’m just saying” Sam looked up to see Dean standing there . He was wearing his jeans and black t-shirt and their dad’s old leather jacket..which only meant one thing..he had been at work. “What are you talking about?” Dean smirked and held up Sam’s cellphone. “Castiel called me..” He walked up to the counter and put the phone down. “You left your phone in the car and..well he wanted to return it. But Gabriel was in meetings all morning so…” He smirked “I wonder if his sister is hot...is she?”

Sam moaned “Dean I’m not setting you up with Anna, for all I know she has a boyfriend..” Dean shrugged “Hey can’t tell me I can’t try.” Sam sighed and looked over at him “Dean I’m not going to let him pay for me to go to college…”

“The hell you’re not! Sammy look, it isn’t often that a hot, rich guy falls for you! So don’t be stupid here! Milk the fucker dry! I mean okay think about it for a second, you say no to Gabriel he’s probably going to still go after you...or he might not. But let’s go with the thought that he isn’t going to keep going after you. So you’ll be single again..working at a coffee shop and what...MAYBE you’ll have the money for the spring semester.”

“Okay, well what about this, if I leave who’s going to help you pay for rent?” Dean laughed at his brothers semantics “Sammy I never needed you in the apartment, I can afford it just fine I just know you’d never afford your own place. Look from what I’ve seen he really cares about you, and you have to care about him a little bit or you wouldn’t be having this morality issue.”

Sam looked at Dean “I might spend the night at his house” Dean shrugged “There’s a start, now do yourself a favour and stop thinking about the logistics. If you like this man, go ahead and give it a hundred and ten percent. What’s the worst that can happen? You don’t like the guy you move back home. You know you always have a room at my place..we might have to have it steam cleaned when you come home...but you always have a place with me, your my brother.”

Sam started to laugh softly and shook his head “You are disgusting” Dean smirked “I pride myself on it, now what does a greasemonkey have to do to get some service?” Sam turned to get his brother’s coffee when Jessica appeared at his side with the coffee and sandwich in hand. “Extra large tripple tripple, turkey sandwich, extra turkey.” Dean smirked “Now see, this is one you should never have let go...I don’t think Gabe’s ever gonna be able to remember my lunch order.”

“Get out of here Winchester” Jessica laughed and Dean winked at the woman and walked out of the shop as Sam pulled out money from his wallet to pay for his order. “You know he says he can afford the place by himself yet I still pay for his meals…” Sam took in a breath “If I can’t keep my job you have to do me a favour, promise you’ll never sleep with him.”

“Me and Dean? Come on Sam, you know I’m better than that. I’m a one Winchester kind of girl”

Sam shook his head and laughed.

\----------------

Sam looked down at his small suitcase, Dean had gone out for drinks after work with a few co-workers so Sam could have some peace and quiet and decide on what he was going to do. Mind you Dead did threaten to put his balls on Sam’s sleeping forehead if the man was still there when he got home. Sam considered this a real threat, because he knew Dean would be pretty drunk when he got home. Closing the suitcase he grabbed his cellphone and sat on his bed and clicked on Gabriel’s name and put the phone to his ear.

“Sammuel” He heard Gabriel’s voice and he smirked.

“Is that how you’re answering the phone now?” Sam looked over at his suitcase and decided that he was going to go through with this. “I’ve made a decision about tonight.”

“I’m already downstairs” Gabriel’s voice cut into Sam’s head and Sam quickly stood up and moved out of his room and through the living room and moved the curtain over the front window and saw Gabriel sitting in his car on the side of the road and Sam blinked “What if I said no?” Gabriel slipped out of his car and looked up at Sam “There was no way you would have said no..”

Sam shook his head and sighed, he wondered if Dean coming to the shop had anything to do with this. Deciding it was better not to be paranoid he smiled “I’ll be down in a minute.”

Sam looked around the living room and took in a breath. “It’s just for the night” He walked through the room and into his own grabbing his small suitcase he turned and walked out of the apartment locking the door behind him.Walking downstairs he pushed open the fire escape door and saw Gabriel standing there and the man gave him a shocked smile “A suitcase Sam?” Sam shook his head “I don’t exactly own a night bag...don’t” He threw his suitcase at the man who caught it and put it into the back of the car. “judge me.” Sam pointed and walked up and gave the man a kiss and Gabriel smirked. “Have you had dinner?”

“Straight to business as always, no I haven’t.” Sam walked around the car and slipped into the passenger seat and looked over at Gabriel when he climbed into the car. “Good I have dinner cooking.” Sam blinked “Aren’t you worried about it burning?” Gabe laughed “No, I might be rich Sam but I still believe in slow cookers.” Sam laughed and held up his hands “I’m sorry I figured you were going to tell me you hired a cook.” Gabriel smiled and lookedb ack out onto the road “I did hire a cook”

Sam shook his head “Unbelievable…”

\------------------

After what could have been the best meal Sam ever ate he was shocked that Gabriel offered a movie as post dinner entertainment. When Sam started laughing Gabriel shook his head “What I’m not aloud to enjoy movies now?” Sam shook his head “No you just keep surprising me...I’m going to go get changed….” Sam paused “Or is that a nono?” Gabriel smirked “Depends on what you wear to bed...I like to be naked” he winked and Sam shook his head “No, I like to wear pj pants and a t-shirt thanks.” Gabriel smirked as Sam walked away “I aim to change that” he called after the taller man.

Gabriel had the movie of choice on, which was Guardians of the Galaxy by the way, by the time Sam walked out of his bedroom.

“You know what, I lied, I like you better in clothes I can pull off with my teeth.” Sam sat down on the couch beside Gabriel and watched the movie. “You are...insane you know that.” 

Gabriel frowned “You don’t trust me?” Sam blinked “Where did that come from?” Sam looked over at Gabriel who shook his head. “I’m wondering if since last night you don’t trust me.” Sam laughed “I trust you, I just haven’t been told that someone wants to pull off my clothes with their teeth before. That’s normally my line” Gabriel looked over Sam “how many ex boyfriends do you have?” The man leaned against the arm of the couch and pulled his legs up beneath him ignoring the tv for the most part. Sam blinked “Wow we’re getting into those questions already? Are you jealous” Gabriel shook his head “No, I just want to understand” Sam blinked “None,” Gabriel nodded “Now I understand, I’m sorry Sam I didn’t know.”

Sam’s jaw tightened “Gabe I don’t get what you’re going about.” Gabe sat up on his knees “You’ve never had sex with - “ “ A man?” Sam cut him off “Yes I have, Gabriel but never a man I cared about….” Gabriel paused and nodded and sat back on his butt and Sam reached forward and grabbed the remote and turned off the t.v, the light from the hallway cast shadows on Sam’s face as he moved closer to him. “If you want me to be a sex crazed teenager I can do that too…” Sam kissed Gabriel’s neck and smirked a little as he kissed around the base of his neck and started to unbutton the man’s shirt. and Gabriel pulled back. “Sam stop….if this is going to be our first time, I need it to be perfect.” Gabriel slipped out from under Sam and pulled the man to his feet. “Come on…” he pulled Sam towards the bedroom for the second time that week. Sam looked down at Gabriel and smiled and kissed his face as soon as they were in the bedroom.

“Don’t pull away this time...promise me?” Gabriel smiled “Believe me kiddo, you’re gonna be begging for an end when I’m done with you.” Sam laughed “Bring it on.” Gabriel smirked “With pleasure”

**Notes for the Chapter:**

> WARNING: The beginning of the next chapter will begin right after the end of this one! Please skip if your not comfortable with fluffy smut. More warnings will be added to the summary of the next chapter.


	11. An almost perfect night

**Summary for the Chapter:**

> Sam and Gabriel have a night together - one that Gabriel hopes to make perfect.

Sam moaned as Gabriel licked up the shaft of Sam and the man fisted the blanket in his hands. His toes curled as Gabriel slipped Sam’s entire length into his mouth. “Gabriel please” he arched his back as Gabriel pulled away and he growled. “I told you I’d have to begging.” Gabriel smirked and crawled up Sam’s body and opened one of the drawers of his left side bed side table and pulled out a small bottle of lube. But before he could move back to Sam, Sam wrapped his arms around the man’s stomach and pulled him over and rolled on top of the man. 

“It’s my turn to make you beg” 

Gabriel looked up at the man and his jaw tightened “What are you doing Sam?” Sam kissed Gabriel’s neck and the man pulled away a little. “Sam you can never make me beg” Using his strength he rolled Sam back over and smirked. “I told you...I wanted to make this perfect” He kissed down Sam’s neck and took the bottle from Sam and poured some of the warm liquid in his hand. “I need you to relax…” he whispered and kissed the man’s face as he covered his fingers and slipped them between Sam’s legs. Gabriel took in a breath as he deepened the kiss with the larger man and slipped a single finger into Sam’s puckered opening. He felt Sam’s body tense around him, and felt Sam gasp into the kiss and he moved his lips to Sam’s ear and nipped at it playfully. “Tell me if I have to stop” He whispered and Sam stayed still and quiet for moment and then rocked his hips slowly upwards. “More...more of you” He breathed and Gabriel kissed the man passionately again and slipped a second finger slowly into Sam and smiled when he heard Sam moan. He slipped his fingers in and out of Sam slowly and moved his lips back down to Sam’s shaking member. Licking his entire length Sam started to shake.

“Gabe...Gabe please I’m ….oh god I’m gonna -” Gabriel didn’t let him finish that sentence when Gabriel quickly crawled back up him and kissed Sam as he pumped his fingers in and out of him. He could tell by the feeling that Gabriel wasn’t going to go much further than that. Not tonight, it wasn’t long until Sam was shaking around beneath him thick velvet ropes covering his stomach.

“Now I need a shower”

Gabe smirked “How about a bath…” Sam pushed himself up onto his elbows and Gabriel was already walking across the room wiping what Sam left from his stomach.

“I haven’t taken a bath since I was five.” Gabriel stopped at the bathroom door and smiled “Then it’s about time you have” Sam flopped backwards and heard water running.

‘You’re serious about this...oh god” Sam pushed himself up and walked into the bathroom and laughed at what he saw. Gabriel was sitting in a large jacuzzi tub already waist deep in bubbled water, candles dotted the room with different shapes and sizes. “Come in , the water’s warm.” Sam smirked and walked across the room and slipped into the tub and smirked when Gabriel quickly slipped into his lap and wrapped his arms around the man’s neck. “I can’t believe you’ll always be mine.” Sam laughed a little and cleared his throat. “Are you uh.” He chuckled nervously “Come on Gabe you don’t know me that well, I wouldn’t get your hopes up yet.” 

Gabe frowned “What’s that supposed to mean?” Sam shook his head “Nothing look come on, let’s have a bath then we’ll head to bed.”

Gabriel shook his head and pulled away. “ No, Sam that isn’t how this works, you signed a contract.” Sam blinked “I’m sorry are you kidding me? I signed a contract saying I wouldn’t tell anyone your precious little business secrets not that I was committing to some sort of ….forced relationship.” Sam pulled himself out of the tub and shook his head “You know I should have seen this coming, I knew you were too good to be true.” 

“Sam get in the tub.” Gabriel looked up at him with dark eyes, Sam looked down at Gabriel and shook his head “Why should I?”

“Because your not giving me a chance to show you that this is worth it.” Sam shook his head and quickly slipped into the tub and pointed his finger at Gabriel. “I need to know what’s going on Gabriel, what is this?”

Gabriel took in a breath “I told you, I need to control everything in my life...and that includes who I’m with.”

“I’m not a whore Gabe, if that’s the case you can take the tuition back.”

Gabriel shook his head “I’m not saying you’re a whore...there are just things that….” Gabriel smiled “Let’s just take a bath.”

\--------------------------------------

When Sam woke up the next day soft smells floated into the room and he realized that Gabriel was no where to be seen. Grabbing a pair of black shorts he pulled them on and ran his hands through his hair smoothing it out catching a glance of himself in the mirror before he peaked his head out of the door and looked around the man’s penthouse. Walking through the lobby room he walked into the kitchen and saw Gabriel, in a pair of black sweat pants in front of the oven.

Sam shook his head and he smiled “You know, when that lady cooked dinner for us yesterday I half expected her to be your maid.” Gabriel looked over his shoulder at the man a little before looking back down at the large omelette that was cooking in the pan. “Her name is Charlie okay, and yeah she’s sort of my maid. She’s also a friend, plus I do believe in giving staff days off...I wanted us to have the house to ourselves so I gave her the day off.” Sam smirked and walked up behind Gabriel and put his chin on his shoulder while he wrapped his arms around the man’s stomach.

“Is that spinach and swiss cheese?” Sam took in a breath and let it out. “Yes it is, I thought you’d need a good breakfast after last night.”

Sam laughed and pulled back. “Okay so, what are we planning on doing then?”

Gabriel looked over at the man “You’ll see”


	12. Another Question left unanswered

**Summary for the Chapter:**

> After a good time with Gabriel and an uncomfortable meal Sam is left with more questions than he's prepared to answer.
> 
> A/N:
> 
> I just want to thank EVERY single person who's been reading my stories for the past year and a half and leaving small little kudos and comments on them. In March of last year I found out I have been pregnant so needless to say I've had quite the journey myself. Now, a year and a half later I'm finally back on my toes with my life so you can expect to see more from me! I love you all passionately!

Sam had been very confused the entire morning, after Gabriel had fed him breakfast the man disappeared to take a shower. What was even more confusing was that he didn’t use the same bathroom they had used together the night before. Sam managed to get himself dressed and looking appropriate, and by that when he stepped out of the shower there was clothes sitting out for him. Getting dressed in the black jeans and the black and green t-shirt over shirt combo he was given Sam stared at himself in the mirror. “What the hell, why is he dressing me.” He muttered to himself and shook his head. Walking out of the bedroom he saw Gabriel, dressed in a pair of black jeans and a dark green jacket with a red plaid shirt underneath.

“So you get to be comfy and I have to wear a green plaid over shirt.”

Gabriel blinked. “I’m sorry, that’s what Castiel got from Dean.”

Sam rolled his eyes “Figured”

Gabriel licked his tongue. “Did you just roll your eyes Sammuel?”

Sam blinked, his eyes going wide “I’m sorry did you just call me Sammuel? I thought we were all past the formalities.” Sam went to walk past him and Gabriel grabbed his arm quite tight. Sam froze, was this about to turn into a fight? He looked down at Gabriel who starred at him quite sharply, almost like a parent would when scolding a child. “You do not roll your eyes in my presence, ever...I’ve beaten lovers for less” His voice was low and sharp, not like the low sultry voice he was used to when Gabriel whispered.

Sam pulled his arm, with all the strength he could muster, out of Gabriel’s grasp. “I’m sorry?”

Gabriel cleared his throat “We really need to get you to read that entire contract, right well now I have a day planned for us. The weekend is always a little more light hearted but first you need to meet Charlie.”

Sam blinked “Your maid? I already -” Gabriel was smiling and Sam realized that it wasn’t what he was talking about at all. Following Gabriel back to his elevator they went straight to the roof. After climbing a small staircase they arrived on the roof and Sam’s jaw dropped.

“Meet echo Charlie tango! This is my helicopter Sam, I thought I could show you the city from a different angle and then perhaps we could go shopping.”

Sam stared at the helicopter and his stomach dropped, what was he getting himself into? A helicopter? Shopping? The man was offering to live with him so and pay for schooling. “Gabriel this is too much.”

“I want you to understand the lifestyle you would have if you were with me. Now Sammel, get into the helicopter “ Gabe looked at Sam and sighed “Please.”

Sam nodded and climbed into the helicopter and tried not to hold his breath, but when he saw how Gabriel handled the helicopter he never felt so safe. Sam looked down on a city that felt so small beneath them and let out a laugh when he thought about it. “We’re so high up, everyone looks so small I’ve never really got to experience this.” Gabriel looked over at him. “Never? Not even to see your folks?” Sam looked back to the window and then back to the golden haired man beside him. “Nah I normally get stuck with alse seats, you kinda just take what you can when you don’t exactly make the money to choose what you want.”

Later that afternoon after the helicopter ride Sam found himself in the middle of Apple store looking at laptops that would cost almost 3 of his paychecks just to buy. He looked over at Gabriel and shook his head “Gabriel I can’t have one of these.” Gabriel blinked “What’s the problem? Are they not good enough for the school work your going to be doing?” Sam sighed “No it’s not that , I can’t afford them and I’m starting to feel a little uncomfortable with all of this. I told you that I wasn’t sure about the school thing and now you’re trying to buy me accessories for school? I mean..” Sam sighed and shook his head and Gabriel nodded.

“I think it’s time we go out for lunch.” Gabriel nodded towards the door and Sam looked down at the laptop he’d love to have but could never afford and followed behind Gabriel. From the apple store it was a quick walk to the dark restaurant and again they were ushered into a dark back room.

“Are we ever going to eat like a normal couple? In a dive with a couple of super good dishes on some really destroyed benches?”

Gabriel blinked “Is that what you want to do?”

Sam sat down and shrugged “I don’t know once in a while it’d be nice to feel like a normal human being.”

Gabriel sat down and pulled the contracts back out from a backpack he had been carrying around with him since they got off the helicopter. “What are those doing here?” Sam saw the large contracts and Gabriel pushed one towards him. “I want you to read it, really read it.” 

 

\------------------------

Sam stared out of the window of his apartment that he shared with his brother and took in a breath. He had called in sick for the past two shifts at the coffee shop and he had told Castiel that if Gabriel tried to send him to his house to leave and just lie to Gabriel and tell the man he wasn’t at home.

“You’re going to have to talk to him at some point.” Dean was staring in the floor length mirror that sat in the hallway just before the door. He was playing with his hair, trying to get it to sit a certain way and then walked back into the livingroom. “Okay tell me again what was so wrong with this contract that he wanted to make you sign? I mean it was just a NDA wasn’t it?”

Sam shook his head and cleared his throat. “No Dean, it wasn’t just a NDA, it had...lists of expectations, disgusting things Dean. I’m not about that kind of thing.”

Dean sighed “So the guy has a bit of a fetish who cares, I mean I’m sure he wasn’t asking you to let him tie you to a bed and fuck your brains out.” When Sam looked up Dean’s eyebrows shot up “Okay well that isn’t that bad anyway.” Dean heard the buzzer go off and he smirked and went to answer it. “I’ll be right down” He spoke into the speaker as he pressed against the button beneath it.

“Hey Dean I have a question” Sam perked up suddenly, Dean looked back at his brother with a questionable look on his face and Sam sighed “When did you realize that you were…”

“Into guys?” Dean finished the question and shrugged “Hey man, it’s the 2010’s men, women, does it even matter anymore? For me it’s all about the pleasure thing, I mean if I meet a guy who can give a killer blow job does it matter?”

Sam rolled his eyes and looked back out the window. “I’ll tell Castiel you said hi.” Dean left the apartment and Sam blinked looking over at the door. Was his brother going on a date with Castiel Novak? 

Standing up he walked over to the computer that just so happen to be delivered to his apartment despite him telling Gabriel that he wanted some space. Opening the computer he opened up a web browser and started to google some items on the contract that didn’t make sense to him. The more he researched the less he wanted into this contract. Half way through his second cup of coffee a small message appeared in the bottom corner of the computer.

‘I thought you were sick, do you tend to use a computer when your sick?’ 

Sam stared at the message and sighed, of course Gabriel would have had all the information on his email and stuff. Shaking his head he cleared his throat as if he were about to talk and then laughed at his own motion.

‘I’m researching, you said this was for school so I’m looking up some stuff’

‘And?’

Sam stared at the computer and closed the computer, he wasn’t ready to answer that question yet.


End file.
